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The Black Sheep’s Guide to Running a March Madness Pool

It’s March, and a constant stream of college basketball on TV has given you insatiable appetite for illegal betting and making money off collegiate athletes. One team wins, one teams loses—what could be so hard about that? You’ve always wondered how to get involved in this March Madness craziness, but you’ve always been scared to ask. Luckily, you’re reading a guide to running your very own March Madness pool, so let’s get started. 

5.) Figure out what this thing is from your local rec center, nearest library, or area sports bookie, Luca: 

Wow, that’s a nice–wait, what exactly is it? You’ve seen these in year’s past, and you’ve always wondered what in the Sam Hill is going on here. Do you write on those lines? You’re embarassed, but goddamnit, you’re going to create the best fucking March Madness pool anyone has ever seen. Try reaching out to your nearest library; Kyle, the three-sport varsity-letter winner from high school; or area bookie, Luca, for answers. 

4.) Area bookie Luca helped you figure out what a bracket is. Now, it’s to get in on that March Madness pool action he’s been hoarding for himself all these years: 

After taking our advice to consult with Luca on what exactly a bracket is, you became intrigued with his business, and you thought to yourself, “Hey, it’s time Luca stopped being such a greedy sonuvabitch this time of year and let me get a slice of that March Madness pool pie.” Sure, he looks jovial, dresses casually, and smokes cigarettes when he’s looking for good conversation, but be warned: Luca has family back in the old country that you do not want to fuck with (within minutes of meeting him, he’s told you so). Stand up straight, be stern in your demands, and get Luca to let you in. 

3.) In your first assignment for Luca, you’re tasked with going door-to-door to “ask” if people are interested in joining Luca’s March Madness pool: 

There’s no turning back now! Luca has asked you to go door-to-door in the neighborhood to “ask” if people are willing to participate in his March Madness pool. (When you’re surrounded on all sides by Paulie “Razor” Ricci, Johnnie Colombo, and Uncle Gio, you just don’t say no to anything.) Luca never said to “shakedown” or “break anyone’s fucking legs” if they didn’t want to particpate, but that doesn’t mean you can’t be persistent! Remember: the more people you get in your March Madness pool, the bigger cut you’re bringing home at the beginning of April. 

2.) Area brothers Rickie and Greg O’Sullivan are in deep to Luca, but they’re hoping that a good run on a big bet in his March Madness pool will get them out of debt for good. Your job? Make sure they don’t skip town: 

Rickie and Greg O’Sullivan went to grade school with Luca’s kids, so Luca’s always had a soft spot for their betting habits. The problem? They’re $60k in debt to Luca and are doubling down on their debt in the March Madness pool as a last-ditch effort to pay off their bad habits and “finally settle down and stop gambling, we swear to fucking God.” They seem sincere, and you’d give them a pass in a former life, but you’re with Luca now–he’s promised you an extra 5% cut if you keep an eye on these guys. 

1.) Keep the peace, collect the bets, take your cut, and don’t you dare fucking lie about a single dime to Luca — one day, you could be running this March Madness pool: 

Sure—you didn’t “run” your own March Madness pool this year, but this ain’t goddamn amateur hour. You gotta put in work to get results, and Luca saw what a brave solide–“associate”–you were, especially taking care of the O’Sullivan brothers ($58,500 ain’t $60k, in any language, in any part of the world). Keep it up, kid—you got a future here. 


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